Phenoxyphenoxy-propionic acid derivatives

ABSTRACT

Phenoxyphenoxy-propionic acid derivatives of the formula ##STR1## exhibit an outstanding herbicidal activity against a wide variety of weed grasses and are well tolerated by dicotyledonous crop plants and various cereals.

The present invention provides novel 2-[4'-phenoxyphenoxy]-propionic acid derivatives of the formula I ##STR2## in which R means identical or different substituents selected from the group consisting of halogen, C₁ -C₄ alkyl or C₁ -C₄ alkoxy,

Y is oxygen or sulfur,

n is 1 or 2

R₁ represents

(a) straight chain or branched C₁ -C₁₂ alkyl substituted once or several times by cyclohexyl, halophenyl, nitrophenyl, C₁ -C₄ alkylphenyl, a radical of the formula ##STR3## or, in 2-position relative to Y or in farther position, by identical or different radicals selected from the group consisting of hydroxy, halogen, thiocyano, or phenyl;

(b) mono- or di-C₁ -C₄ alkylcyclohexyl;

(c) cyclohexenyl or C₃ -C₄ alkenyl substituted by halogen, hydroxy, phenyl, halophenyl, or C₁ -C₄ alkylphenyl;

(d) naphthyl or phenyl which may be substituted once or twice by C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, CF₃, NO₂, CN, SCN, CHO, C₁ -C₃ alkoxy, C₁ -C₃ alkoxycarbonyl, aminocarbonyl, di-C₁ -C₄ alkylamino, C₁ -C₂ alkylthio and may additionally contain halogen;

furthermore, in the case of Y being oxygen,

(e) linear or branched C₃ -C₆ alkinyl, optionally mono- or disubstituted by C₁ -C₄ alkyl, C₁ -C₄ alkoxy, halogen, phenyl, halophenyl, or C₁ -C₄ alkylphenyl;

(f) halocyclohexyl optionally substituted by C₁ -C₄ alkyl;

(g) a radical of the formula ##STR4## (h) C₁ -C₂ alkyl substituted by furyl, tetrahydrofuryl, pyridyl, or oxiranyl;

(i) C₂ -C₄ alkyl substituted by 3 to 7 chlorine and/or fluorine atoms;

and, in the case of Y being sulfur,

(k) C₃ -C₄ alkenyl;

R₂ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, hydroxyethyl, or chloroethyl;

R₃ is hydrogen, C₁ -C₄ alkyl, chloroethyl, phenyl, halophenyl, C₁ -C₄ alkylphenyl, hydroxyethyl, or aliphatic C₁ -C₄ acyl;

R₂ and R₃ together may represent a saturated or unsaturated hydrocarbon chain having 2, 4, or 5 members in which one carbon atom may be replaced by --O--, --CO--, --N═, --NH-- or --N--C₁ --C₄ alkyl;

R₄ is hydrogen or C₁ -C₄ alkyl;

Z represents the anion of an inorganic or organic acid;

R₁ ' is linear or branched C₁ -C₁₂ alkylene;

R₅ represents C₁ -C₆ alkyl, C₁ -C₄ haloalkyl, C₂ -C₈ alkoxyalkyl, C₃ -C₁₂ alkoxyalkoxyalkyl, hydroxyethyl, or phenyl which may be substituted once or twice by halogen and/or C₁ -C₃ alkyl;

R₆ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, phenyl optionally substituted by halogen, nitro and/or C₁ -C₄ alkyl, or a radical of the formula ##STR5## R₇ is C₁ -C₄ alkyl, phenyl, halophenyl, nitrophenyl, or C₁ -C₄ -alkylphenyl;

R₈ stands for hydrogen, C₁ -C₄ alkyl, or C₁ -C₄ alkoxy;

R₉ is C₁ -C₄ alkyl and

p means zero or 1 or 2, and salts thereof with bases.

The following are examples of radicals of the formula ##STR6## in which R₂ and R₃ together form a closed chain: ##STR7##

Radicals of the aforesaid type can also be contained in the radicals of formulae III and IV.

Preferred halogen atoms are fluorine, chlorine and/or bromine and Z preferably stands for Cl-, Br-, HSO₄ -, methanesulfonate, ethane-sulfonate, p-toluene-sulfonate, acetate and trichloroacetate.

Especially preferred are those compounds of formula I in which

(R)_(n) represents 1 or 2 halogen atoms, preferably Cl or Br in 4- and/or 2-position;

Y is oxygen;

R₁ means

(a) linear or branched C₁ -C₈ alkyl which is mono- or disubstituted by cyclohexyl, halophenyl, C₁ -C₄ alkylphenyl, a radical of formula II, III or IV, or in 2-position or a position more remote from Y, by hydroxy or halogen;

(b) halocyclohexyl, C₁ -C₄ alkylcyclohexyl;

(c) cyclohexenyl, halo-C₃ -C₄ -alkenyl, hydroxy-C₃ -C₄ -alkenyl, or phenyl-C_(3-C) ₄ alkenyl;

(d) C₃ -C₆ alkinyl mono- or disubstituted in 1-position by C₁ -C₄ alkyl, phenyl, halophenyl, or C₁ -C₂ alkylphenyl, 4-halobutin-2-yl, C₁ -C₂ alkoxybutin-2-yl;

(e) a radical of one of the formulae V, VI, VII, IX, X and XII;

(f) phenyl optionally substituted by C₁ -C₄ alkyl, CF₃, NO₂, C₁ -C₃ alkoxy, C₁ -C₃ alkoxycarbonyl, or dimethylamino and possibly containing additionally 1 or 2 chlorine or bromine atoms;

(g) a radical of one of the formulae ##STR8## (h) trifluoroethyl, tetrafluoropropyl, or pentafluoropropyl; R₂ is hydrogen, C₁ -C₄ alkyl or chloroethyl;

R₃ is hydrogen, C₁ -C₄ alkyl, chloroethyl, phenyl, halophenyl, C₁ -C₄ alkylphenyl, or aliphatic C₁ -C₄ acyl;

R₁ ' represents linear or branched C₁ -C₈ alkylene;

R₅ is C₁ -C₆ alkyl, C₁ -C₄ haloalkyl, C₁ -C₆ alkoxyethyl, C₁ -C₆ alkoxyethoxyethyl, hydroxyethyl, phenyl optionally mono- or disubstituted by halogen and/or C₁ -C₃ alkyl;

R₆ represents C₁ -C₄ alkyl, C₁ -C₂ haloalkyl, phenyl optionally substituted by halogen and/or C₁ -C₂ alkyl, or a radical of on of the formulae ##STR9## R₇ stands for C₁ -C₄ alkyl, phenyl, chlorophenyl, or C₁ -C₂ -alkylphenyl;

R₈ is hydrogen or C₁ -C₄ alkyl and

R₂ +R₃, R₄, R₉, Z and p have the above meanings.

In the case of Y being sulfur R₁ preferably represents C₁ -C₆ haloalkyl or C₃ -C₄ alkenyl.

The compounds of formula I according to the invention may be prepared by the following methods:

(a) By reacting 2-[4'-phenoxyphenoxy]-propionic acid halides of formula XIII, which are readily accessible by halogenating correspondingly substituted 2-[4'-phenoxyphenoxy]-propionic acids, with hydroxy- or thio-compounds of formula XIV, in the presence or absence of acid-binding agents, the compounds of formula I are obtained according to the following equation: ##STR10##

The reaction is carried out in aprotic solvents, for example a hydrocarbon such as toluene and benzene; a halohydrocarbon such as methylene chloride; an aliphatic carboxylic acid nitrile such as acetonitrile; and ethers such as tetrahydrofurane, preferably, however, in benzene or toluene, at a temperature in the range of from -20° C. to the boiling point of the solvent used. Suitable acid-binding agents are preferably tertiary amines such as triethylamine and pyridine.

When compounds of formula XIV are used in which the radical R₁ is substituted by a radical of formula II or III, the reaction can be carried out without acid-binding agents. Especially when R₂ and/or R₃ represent hydrogen, the compounds of formula XIV are reacted in the form of the hydrohalide in order to avoid N-acylation.

In the case of R₁ in formula XIV representing a substituted aryl radical, the compounds of formula I are preferably prepared according to the aforedescribed method.

(b) Alternatively, the compounds of formula I can be prepared by esterification of a compound of formula XIV with an optionally substituted 2-[4'-phenoxyphenoxy]-propionic acid, preferably with the addition of an acid catalyst, for example concentrated sulfuric acid or toluenesulfuric acid, in the presence of an organic solvent forming an azeotrope with water such as chloroform or benzene.

(c) Compounds of formula I in which Y is oxygen can also be prepared by reacting a salt of a correspondingly substituted 2-[4'-phenoxyphenoxy]-propionic acid with a substituted halogen compound of formula XV: ##STR11##

Suitable solvents are preferably polar solvents such as dimethyl formamide, aliphatic alcohols and aliphatic ketones, as well as an excess of the compounds of formula XV. The reaction is preferably carried out at a temperature in the range of from room temperature to the boiling point of the solvent used.

(d) Compounds of formula I can also be obtained by alkylation of correspondingly substituted 4-phenoxyphenols of formula XVI with substituted propionic acid esters of formula XVII under basic conditions: ##STR12## In the equation W represents a halogen atom, preferably bromine or chlorine, or a sulfonic ester radical such as the tosylate or mesylate group. Suitable solvents are ketones such as acetone or ethylmethyl ketone; dimethyl formamide, dimethyl sulfoxide, acetonitrile, or aromatic hydrocarbons such as toluene. To bind the liberated acid tertiary amines such as triethylamino or pyridin, or alkali metal carbonates such as potassium carbonate or soda are used.

(e) Other compounds of formula I can be obtained by transforming compounds of formula I obtained in the first stage, for example by the addition of halogen, hydrogen halide or water, to compounds of formula I containing olefinic double bonds or triple bonds, by nucleophilic substitution in compounds with halogen-substituted ester group, by oxidation of compounds with thioalkylated ester groups, by alkylation and acylation of hydroxy-substituted compounds.

The compounds according to the invention exhibit a strong herbicidal activity against a wide variety of weed grasses, and are well tolerated by dicotyledonous crop plants and various cereals. Hence, they can be used for selectively combating weed grasses even in crop plants.

It is, therefore, another object of the present invention to provide herbicidal compositions containing the compounds of formula I as active ingredient besides the usual formulation auxiliaries and inert materials, and a further object is the use of the compounds of formula I for controlling weed grasses.

The herbicidal compositions according to the invention generally contain 2 to 95% of an active compound of formula I. They can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules, in admixture with the usual formulation auxiliaries.

Wettable powders are preparations that can be uniformly dispersed in water and contain, besides the active ingredient, a diluent or an inert substances, a wetting agent, for example polyoxethylated alkylphenols, or polyoxethylated oleyl- or stearyl-amines, alkyl- or alkyl-phenyl-sulfonates, and dispersing agents, for example the sodium salt of lignin-sulfonic acid, of 2,2'-dinaphthylmethane-6,6'-disulfonic acid, or sodium oleylmethyl-tauride.

Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or aromatic hydrocarbons having a higher boiling point.

Dusting powders are obtained by grinding the active ingredient with finely divided, solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite, or diatomaceous earths.

Spraying solutions, commercially available as aerosol sprays, contain the active ingredient dissolved in an organic solvent, and in addition thereto a propellant, for example a mixture of fluorochlorohydrocarbons and/or carbon dioxide.

Granules can be produced by atomizing the active ingredient on to an adsorptive, granulated inert material, or by applying concentrates of the active ingredient to the surface of a support, for example sand, kaolinite or a granulated inert material, with the aid of an adhesive, for example polyvinyl alcohol, the sodium salt of polyacrylic acid, or mineral oils. Alternatively, suitable active ingredients may be made into granules, if desired in admixture with fertilizers, in the manner commonly used for the manufacture of granulated fertilizers.

The commercial herbicidal preparations contain varying concentrations of the active ingredients. In wettable powders the concentration of active ingredient varies, for example, from about 10 to 95%, the remainder being the above formulation additives. Emulsion concentrates contain about 10 to 80% of active ingredient, while dusting powders mostly contain 5 to 20% of active ingredient and sprayable solutions about 2 to 20%. In the case of granules, the content of active ingredient partly depends on whether the active ingredient is liquid or solid and on the type of granulation auxiliary or filler used.

For application the commercial concentrates are optionally diluted in usual manner, the wettable powder or emulsifiable concentrate, for example with water. Dusts and granulated formulations as well as sprayable solutions are not diluted further with an inert substance before their application. The amount applied varies with the external conditions, such as temperature, humidity and the like. The applied amounts can vary within wide limits, for example in the range of from 0.1 to 10.0 kg per hectare, preferably from 0.1 to 3 kg per hectare.

The active compounds of the invention can be mixed with other herbicides and soil insecticides.

The following examples illustrate the invention.

FORMULATION EXAMPLES EXAMPLE A

An emulsifyable concentrate is obtained from

15 parts by weight of active substance

75 parts by weight of cyclohexanone as solvent and

10 parts by weight of oxethylated nonylphenol (10AeO) as emulsifier.

EXAMPLE B

A dusting powder is obtained by mixing

10 parts by weight of active substance

90 parts by weight of talcum as inert substance and grinding the mixture obtained in a cross-beater mill.

EXAMPLE C

A wettable powder which is readily dispersible in water is obtained by mixing

25 parts by weight of active substance

64 parts by weight of kaolin-containing quartz as inert substance

10 parts by weight of the potassium salt of lignin-sulfonic acid

1 part by weight of sodium oleylmethyl tauride as wetting and dispersing agent, and grinding the mixture obtained in a disk attrition mill.

EXAMPLE D

A granulate consists, for example, of approximately

2 to 15 parts by weight of active substance and

98 to 85 parts by weight of inert granular carrier material, for example attapulgite, pumic and quartz sand.

EXAMPLES OF PREPARATION EXAMPLE 1: (process A) 2-[4'-(2",4"-dichlorophenoxy)-phenoxy]-propionic acid 2-chloroeth-1-yl-ester

A solution of 0.06 mol=20.73 g of 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid chloride, prepared from 2-[4'-2",4"-dichlorophenoxy)phenoxy]-propionic acid and thionyl chloride, in 60 ml absolute toluene was added dropwise at room temperature to a solution of 0.06 mol=4.83 g of ethylene chlorohydrin (2-chloroethanol) and 0.06 mol=6.06 g of triethylamine in 60 ml absolute toluene. After the addition, stirring of the mixture was continued for 1 hour at 50° C., the precipitated triethylamine chloride was filtered off, and the filtrate was washed with dilute sodium hydroxide solution and with water. The toluene solution was dried over sodium sulfate and the solvent was distilled off under reduced pressure. 21.25 g=91% of the theory of 2-[4'-(2",4"-dichlorophenoxy)-phenoxy]-propionic acid 2-chloroeth-1-yl ester were obtained having a refractive index n_(D) ²⁴ of 1.5672. ##STR13##

EXAMPLE 2: (process B) 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid 2-methoxyeth-1-yl ester

0.1 mol=22.05 g of 4-(4'-chlorophenoxyphenol) and 0.1 mol=13.8 g of potassium carbonate in 100 ml dimethyl formamide were heated for 2 hours at 100° C., whereupon 0.1 mol=21.1 g of 2-bromopropionic acid 2-methoxyeth-1-yl ester was added dropwise at 60° C. and the mixture was stirred for 6 hours at 120° C. After filtration of the precipitated salt, the solvent was distilled off under reduced pressure and the residue fractionated in a high vacuum. 28.7 g=82% of the theory of 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid 2-methoxyeth-1-yl ester were obtained having a boiling point of 176° C. under 0.05 torr and a refractive index n_(D) ²⁵ of 1.5460. ##STR14##

EXAMPLE 3: (process C) 2-[4'-(2",4"-dichlorophenoxy)-phenoxy]-propionic acid glycol semi-ester

0.4 mol=131 g of 2-[4'-(2",4"-dichlorophenoxy)-phenoxy]-propionic acid were neutralized with 400 ml 1 N sodium hydroxide solution. The water was distilled off under reduced pressure, 200 ml ethylene chlorohydrin (2-chloroethanol) were added to the sodium salt of 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid and the suspension was refluxed for 3 hours. After distillation of the excess ethylene chlorohydrin under reduced pressure, the residue was repeatedly extracted with toluene, the solvent was distilled off and the oily residue distilled in a high vacuum. 128.2 g=86% of the theory of 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid glycol semi-ester were obtained boiling at 232° C. under 0.04 torr. ##STR15##

EXAMPLE 4: (process D) 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid 4-chlorobut-1-yl ester

24.4 g=0.08 mol of 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid, 10.8 g=0.1 mol of 4-chlorobutanol and 2 ml concentrated sulfuric acid in 50 ml chloroform were refluxed for 6 hours with azeotropic distillation of the reaction water. After cooling, the reaction mixture was washed twice with 100 ml water, neutralized with bicarbonate solution and washed with water until it was free from salt. After drying over calcium chloride and distillation of the solvent, 27.0 g=88% of the theory of 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid 4-chlorobut-1-yl ester were obtained having a refractive index n_(D) ²⁴ of 1.5517. ##STR16##

EXAMPLE 5 (process A) 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid-2-pyrrolidino-eth-1-yl ester hydrochloride

0.06 mol=20.73 g of 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid chloride dissolved in 30 ml absolute toluene were added dropwise at room temperature to a solution of 0.06 mol=6.9 g of 2-pyrrolidino-ethanol in 50 ml absolute toluene and the mixture was stirred for a further hour at 60° C. After cooling to 0° C., the formed precipitate was filtered off and recrystallized from acetone. 21.0 g=76% of the theory of 2-[4'-(2",4"-dichloro-phenoxy)phenoxy]-propionic acid 2-pyrrolidino-eth-1-yl ester hydrochloride were obtained melting at 160°-162° C. ##STR17##

EXAMPLE 6: (process E) 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid 2-dimethyl-amino-eth-1-yl ester

0.8 mol=24.8 g 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid chloride dissolved in 30 ml toluene was added dropwise at room temperature to a solution of 0.08 mol=7.12 g of 2-dimethylamino-ethanol in 50 ml absolute toluene. After the addition, the reaction mixture was stirred for 1 hour at 50° C. After washing with water, the organic phase was dried over sodium sulfate. After elimination of the solvent, the remainder was fractionated. 25.5 g=88% of the theory of 2-[4'-(4"-chlorophenoxy)phenoxy]-propionic acid 2-dimethyl-aminoeth-1-yl ester were obtained boiling at 182° C. under 0.1 torr. ##STR18##

EXAMPLE 7: (process F) 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid 2-methylsulfinyl-eth-1-yl ester

A solution of 3-chloroperbenzoic acid (11.95 of commercial product of 65% strength) in 50 ml chloroform was added dropwise at -20° C. to a solution of 18 g=0.045 mol of 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid 2-methylmercapto-eth-1-yl ester (Example 52) in 50 ml chloroform. After the addition, the reaction mixture was stirred for a further 2 hours at -20° C. After filtration of the precipitate of 3-chlorobenzoic acid, the organic phase was washed with sodium bicarbonate solution and water and dried over sodium sulfate. After distillation of the solvent under reduced pressure, 17.1 g=91% of the theory of 2-[4'-(2",4"-dichlorophenoxy)phenoxy]-propionic acid 2-methylsulfinyl-eth-1-yl ester were obtained having a refractive index n_(D) ²³ of 1.5781. ##STR19##

Using a 2.2 fold excess of 3-chloroperbenzoic acid there was obtained in analogous manner at room temperature the corresponding sulfonyl compound (Example 53).

The following Table lists further compounds of the invention and the process by which they were prepared.

                                      TABLE                                        __________________________________________________________________________      ##STR20##                                                                     Example                                                                             (R).sub.n                                                                            Y  R.sub.1                          m.p./b.p./n.sub.D                                                                         Variant              __________________________________________________________________________     8    4-Cl  O  CH.sub.2CH.sub.2 Cl              m.p. 48° C.                                                                        A                    9    4-Br-2-Cl                                                                            O  CH.sub.2CH.sub.2 Cl              n.sub.D.sup.20                                                                            A 1.5715             10   4-Cl  O  CH.sub.2CH.sub.2CH.sub.2 Cl      b.p..sub.0.1                                                                              A 188°        11   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2CH.sub.2 Cl      b.p..sub.0.02                                                                  = 186°                                                                             A                    12   4-Cl  O  CH(CH.sub.3)CH.sub.2 Cl          n.sub.D.sup.24                                                                            A 1.5514             13   4-Cl  O  CH(CH.sub.2 Cl).sub.2            n.sub.D.sup.24                                                                            A 1.5568             14   4-Br-2-Cl                                                                            O  CH(CH.sub.3)CH.sub.2 Cl          n.sub.D.sup.20                                                                            A 1.5665             15   4-Br-2-Cl                                                                            O  CH(CH.sub.2 Cl).sub.2            n.sub.D.sup.20                                                                            A 1.5752             16   4-Cl  O  CH.sub.2CH.sub.2 Br              m.p. 56°-57°                                                     C.         A                    17   4-Cl  O  CHCHBrCH.sub.2 Br                n.sub.D.sup.24                                                                            A 1.5806             18   2-Br-4-Cl                                                                            O  CH.sub.2CH.sub.2 Br                         A                    19   2-Br-4-Cl                                                                            O  CH.sub.2CHBrCH.sub.2 Br                     A                    20   4-Cl  O  CH.sub.2CHClCH.sub.2 Cl          n.sub.D.sup.23                                                                            A 1.5581             21   2,4-Cl.sub.2                                                                         O  CH.sub.2CHBrCH.sub.2 Br          n.sub.D.sup.23                                                                            A 1.5856             22   2,4-Cl.sub.2                                                                         O  CH.sub.2CHClCH.sub.2 Cl          n.sub.D.sup.23                                                                            A 1.5750             23   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2 Br              n.sub.D.sup.24                                                                            A 1.5750             24   2,4-Cl.sub.2                                                                         O  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                                          n.sub.D.sup.25                                                                            A 1.5562             25   2,4-Cl.sub.2                                                                         O  CH.sub.2(CH.sub.2).sub.4CH.sub.2 Cl         A                    26   2,4-Cl.sub.2                                                                         O  CH(CH.sub.2 Cl).sub.2            n.sub.D.sup.24                                                                            A 1.5679             27   2,4-Cl.sub.2                                                                         O  CH(CH.sub.3)CH.sub.2 Cl          n.sub.D.sup.24 =                                                                          A.5610               28   2,4-Cl.sub.2                                                                         O  CH.sub.2 CF.sub.3                m.p. 45° C.                                                                        A                    29   2,4-Cl.sub.2                                                                         O  CH.sub.2CF.sub.2CF.sub.2 H       n.sub.D.sup.23                                                                            A 1.5219             30   2,4-Cl.sub.2                                                                         O  CH.sub.2CF.sub.2CF.sub.3         n.sub.D.sup.23                                                                            A 1.5047             31   4-Cl  O  CH.sub.2CF.sub.3                 m.p. 52°-53°                                                     C.         A                    32   4-Cl  O  CH.sub.2CF.sub.2CF.sub.2 H       n.sub.D.sup.24                                                                            A 1.5135             33   4-Cl  O  CH.sub.2CF.sub.2CF.sub.3         n.sub.D.sup.24                                                                            A 1.4952             34   4-Br-2-Cl                                                                            O  CH.sub.2CF.sub.3                 n.sub.D.sup.25                                                                            A 1.5349             35   4-Br-2-Cl                                                                            O  CH.sub.2CF.sub.2CF.sub.2 H                  A                    36   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2OCH.sub.3        n.sub.D.sup.24                                                                            B 1.5540             37   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2CH(CH.sub.3)OCH.sub.3                                                                           n.sub.D.sup.25                                                                            A 1.5457             38   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2OCH.sub.2CH.sub.3           A                    39   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2 OCH.sub.2CH.sub.2 Cl                                                                           b.p..sub.0.07 :                                                                203° C.                                                                            A                    40   2,4-Cl.sub.2                                                                         O                                                                                  ##STR21##                       n.sub.D.sup.24                                                                            A 1.5612             41   2,4-Cl.sub.2                                                                         O                                                                                  ##STR22##                                  A                    42   2,4-Cl.sub.2                                                                         O                                                                                  ##STR23##                       n.sub.D.sup.24                                                                            A 1.5678             43   2,4-Cl.sub.2                                                                         O                                                                                  ##STR24##                       n.sub.D.sup.25                                                                            A 1.5793             44   2,4-Cl.sub.2                                                                         O                                                                                  ##STR25##                       n.sub.D.sup.25                                                                            D 1.5712             45   2,4-Cl.sub.2                                                                         O                                                                                  ##STR26##                       n.sub.D.sup.25                                                                            A 1.5971             46   2,4-Cl.sub.2                                                                         O                                                                                  ##STR27##                       n.sub.D.sup.29,5 =                                                                        A.5804               47   2,4-Cl.sub.2                                                                         O                                                                                  ##STR28##                                  A                    48   2,4-Cl.sub.2                                                                         O                                                                                  ##STR29##                       n.sub.D.sup.29,5 =                                                                        A.5695               49   2,4-Cl.sub.2                                                                         O                                                                                  ##STR30##                                  A                    50   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH         C                    Example                                                                             (R).sub.n                                                                            Y  R.sub.1                          m.p./b.p./n.sub.D /analysis                                                    .          Variant              __________________________________________________________________________     51   2,4Cl.sub.2                                                                          O  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCH.sub.3  A                    52   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2SCH.sub.3        n.sub.D.sup.24                                                                            A 1.5682             53   2,4-Cl.sub.2                                                                         O                                                                                  ##STR31##                       n.sub.D.sup.23                                                                            F 1.5670             54   4-Cl  O  CH.sub.2CH.sub.2CH(CH.sub.3)OCH.sub.3                                                                           n.sub.D.sup.24                                                                            A 1.5367             55   4-Cl  O  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OCH.sub.3                                                                     C 60.8 60.8                                                                               A                                                                   H  5.9  6.1                                                                               A                    56   4-Cl  O  CH.sub.2CH.sub.2OH                          C                    57   4-Cl  O  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH                                                                             C 59.8 60.4                                                                               C                                                                   H  5.6  5.6                     58   4-Cl  O  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2Cl                                                                             b.p..sub.0.01 :                                                                208° C.                                                                            A                    59   4-Cl  O  CH.sub.2CH(OH)CH.sub.2OH . H.sub.2 O                                                                            m.p. 52°-53°                                                     C.         C                    60   4-Cl  O                                                                                  ##STR32##                       n.sub.D.sup.25                                                                            A 1.5600             61   4-Cl  O                                                                                  ##STR33##                       C 64.3 64.6 H  4.6                                                                        A.5                  62   4-Cl  O                                                                                  ##STR34##                       n.sub.D.sup.29.5 =                                                                        A.577                63   4-Cl  O                                                                                  ##STR35##                                  A                    64   4-Cl  O  CH.sub.2CH.sub.2SCH.sub.3        n.sub.D.sup.24                                                                            A 1.5678             65   4-Br-2-Cl                                                                            O  CH.sub.2CH.sub.2OH                          C                    66   4-Br-2-Cl                                                                            O  CH.sub.2CH.sub.2OCH.sub.3                   A                    67   2,4-Cl.sub.2                                                                         O                                                                                  ##STR36##                                                       68   2,4-Cl.sub.2                                                                         O                                                                                  ##STR37##                                                       69   4-Cl  O                                                                                  ##STR38##                       C 65.7  65.4 H  4.75  4.9                                                      N  3.65  3.7                                                                              A                    70   4-Cl  O                                                                                  ##STR39##                       b.p..sub.0.1 : 210°                                                     C.         A                    71   4-Cl  O  CH(C.sub.5 H.sub.11).sub.2       b.p..sub.0.03 :                                                                202°-203°                                                                   A.                   72   2,4-Cl.sub.2                                                                         O                                                                                  ##STR40##                       n.sub.D.sup.25                                                                            A 1.5526             73   2,4-Cl.sub.2                                                                         O                                                                                  ##STR41##                                  A                    74   2,4-Cl.sub.2                                                                         O                                                                                  ##STR42##                                  A                    75   2,4-Cl.sub.2                                                                         O                                                                                  ##STR43##                                  A                    76   2,4-Cl.sub.2                                                                         O                                                                                  ##STR44##                                  A                    77   2,4-Cl.sub.2                                                                         O                                                                                  ##STR45##                       m.p. 60°-61°                                                     C.         A                    78   2,4-Cl.sub.2                                                                         O                                                                                  ##STR46##                       m.p. 60°-61°                                                     C.         A                    79   2,4-Cl.sub.2                                                                         O                                                                                  ##STR47##                       n.sub.D.sup.25                                                                            A 1.5861             80   2,4-Cl.sub.2                                                                         O                                                                                  ##STR48##                       m.p. 104° C.                                                                       A                    81   2,4-Cl.sub.2                                                                         O                                                                                  ##STR49##                       m.p. 68° C.                                                                        A                    82   2,4-Cl.sub.2                                                                         O                                                                                  ##STR50##                       b.p..sub.0.004 :                                                               208° C.                                                                            E                    83   2,4-Cl.sub.2                                                                         O                                                                                  ##STR51##                       n.sub.D.sup.25                                                                            E 1.5141             84   4-Cl  O                                                                                  ##STR52##                       n.sub.D.sup.25.5 =                                                                        E.5552               85   2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2N.sup.⊕ (CH.sub.3).sub.3 J.sup.-                                                                       A                    86   4-Cl  O  CH.sub.2CH.sub.2N(C.sub.2 H.sub.5).sub.2                                                                        n.sub.D.sup.24                                                                            E 1.5407             87   4-Cl  O                                                                                  ##STR53##                       n.sub. D.sup.23                                                                           E 1.5498             88   4-Cl  S                                                                                  ##STR54##                                  A                    89   4-Cl  S  CH.sub.2CHCH.sub.2                          A                    90   2,4-Cl.sub.2                                                                         S  CH.sub.2CHCH.sub.2                          A                    91   4-Br-2-Cl                                                                            O                                                                                  ##STR55##                                  E                    92   4-Br-2-Cl                                                                            O  CH.sub.2CH.sub.2SCH.sub.3                   A                    93   4-Br-2-Cl                                                                            O                                                                                  ##STR56##                                  A                    94   4-Cl  O                                                                                  ##STR57##                       n.sub.D.sup.24                                                                            A 1.5567             95   2,4-Cl.sub.2                                                                         O                                                                                  ##STR58##                       n.sub.D.sup.24                                                                            A 1.5648             96   2,4-Cl.sub.2                                                                         O  CH.sub.2 CCH                     n.sub.D.sup.23                                                                            A 1.5649             97   2,4-Cl.sub.2                                                                         O  CH(CH.sub.3) CCH                 b.p..sub.0.01 :                                                                175°                                                                               A.                   98   2,4-Cl.sub.2                                                                         O  C(CH.sub.3).sub.2 CCH                       A                    99   2,4-Cl.sub.2                                                                         O                                                                                  ##STR59##                       n.sub.D.sup.25                                                                            A 1.5564             100  2,4-Cl.sub.2                                                                         O  CH(C.sub.2 H.sub.5) CCH                     A                    101  2,4-Cl.sub.2                                                                         O                                                                                  ##STR60##                       n.sub.D.sup.23                                                                            A 1.5808             102  4-Cl  O  CH.sub.2 CCH                     m.p. 62.5° C.                                                                      A                    103  4-Cl  O  CH(CH.sub.3)C CH                 b.p..sub.0.05 :                                                                184° C.                                                                            A                    104  4-Cl  O                                                                                  ##STR61##                       n.sub.D.sup.24                                                                            A 1.5449             105  4-Cl  O  C(CH.sub.3).sub.2 CCH                       A                    106  4-Cl  O  CH(C.sub.2 H.sub.5 )CCH          n.sub.D.sup.25,5 =                                                                        A.5462               107  4-Cl  O                                                                                  ##STR62##                       n.sub.D.sup.23                                                                            A 1.5784             108  4-Br-2-Cl                                                                            O  CH.sub.2 CCH                                A                    109  2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2OCH.sub.2(CH.sub.2).sub.2CH.sub.3                                                               b.p..sub.0.005 :                                                               191° C.                                                                            A                    110  2,4-Cl.sub.2                                                                         O  CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2OCH.sub.2 (CH.sub.2).sub.                   2 CH.sub.3                                  A                    111  4-Cl  O  CH.sub.2CH.sub.2OCH.sub.2 (CH.sub.2).sub.2CH.sub.3                                                              b.p..sub.0.05 :                                                                202° C.                                                                            A                    112  4-Cl  O  CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2OCH.sub.2 (CH.sub.2).sub.                   2 CH.sub.3                                  A                    113  4-Br-2-Cl                                                                            O  CH.sub.2CH.sub.2OCH.sub.2(CH.sub.2).sub.2CH.sub.3                                                                          A                    114  2,4-Cl.sub.2                                                                         O                                                                                  ##STR63##                                  A                    115  2,4-Cl.sub.2                                                                         O                                                                                  ##STR64##                       n.sub.D.sup.24.5 =                                                                        A.5661               116  2,4-Cl.sub.2                                                                         O                                                                                  ##STR65##                       n.sub.D.sup.25                                                                            A 1.5606             117  4-Cl  O                                                                                  ##STR66##                       m.p. 76°-77°                                                     C.         A                    118  2,4-Cl.sub.2                                                                         O                                                                                  ##STR67##                       n.sub.D.sup.21                                                                            A 1.5682             119  4-Cl  O                                                                                  ##STR68##                       b.p..sub.0.01 :                                                                234° C.                                                                            A                    120  2,4-Cl.sub.2                                                                         O                                                                                  ##STR69##                       b.p..sub.0.02 :                                                                212° C.                                                                            A                    121  4-Cl  O                                                                                  ##STR70##                       b.p..sub.0.006 :                                                               182° C.                                                                            A                    122  4-Cl  O                                                                                  ##STR71##                                  E                    123  2,4-Cl.sub.2                                                                         O                                                                                  ##STR72##                                  E                    124  2,4-Cl.sub.2                                                                         O                                                                                  ##STR73##                       n.sub.D.sup.28.5 =                                                                        E.5590               125  4-Cl  O  CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                               b.p..sub.0.007 :                                                               186° C.                                                                            A                    126  2,4-Cl.sub.2                                                                         O  CH.sub. 2CH.sub.2OCH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                              b.p..sub.0.005 :                                                               194° C.                                                                            A                    127  2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2(OCH.sub.2 CH.sub.2).sub.2OCH.sub.3                                                             b.p..sub.0.004 :                                                               209° C.                                                                            A                    128  2,4-Cl.sub.2                                                                         O  CH.sub.2CH.sub.2(OCH.sub.2CH.sub.2).sub.2OC.sub.2 H.sub.5                                                                  A                    129  2,4-Cl.sub.2                                                                         O  CH.sub.2CHClCH.sub.3             n.sub.D.sup.29.5 =                                                                        A.5585               130  2,4-Cl.sub.2                                                                         O  CH.sub.2CHBrCH.sub.3             n.sub.D.sup.24.5 =                                                                        A.5686               131  4-Cl  O  CH.sub.2CHBrCH.sub.3             n.sub.D.sup.24.5 =                                                                        A.5627               132  4-Cl  O  CH.sub.2CHClCH.sub.3             n.sub.D.sup.29.5 =                                                                        A.5521               133  2,4-Cl.sub.2                                                                         O                                                                                  ##STR74##                       m.p.: 59-60                                                                               A                    134  2-Cl-4 Br                                                                            O  CH.sub.2CH.sub.2CH(CH.sub.3)OCH.sub.3       A                    135  4-Cl  O                                                                                  ##STR75##                                  A                    136  4-Cl  O  CH.sub.2CH.sub.2OC.sub.2 H.sub.5            A                    137  4-Cl  O  (CH.sub.2CH.sub.2 O).sub.2CH.sub.2(CH.sub.2).sub.4CH.sub.3                                                      b.p..sub. 0.015 :                                                              224° C.                                                                            A                    138  2,4-Cl.sub.2                                                                         O  (CH.sub.2CH.sub.2 O).sub.2CH.sub.2(CH.sub.2).sub.4CH.sub.3                                                      n.sub.D.sup.24                                                                            A 1.5300             139  4-Cl  O  (CH.sub.2 CH.sub.2 O).sub.3CH.sub.3                                                                             b.p..sub. 0.01 :                                                               209° C.                                                                            A                    140  4-Cl  O                                                                                  ##STR76##                       n.sub.D.sup.26                                                                            E 1.5519             141  4-Cl  O                                                                                  ##STR77##                                  A                    142  4-Cl  O  CH.sub.2(CH.sub.2).sub.4CH.sub.2 Cl         A                    143  4-Cl  O  CH.sub.2CCCH.sub.2 Cl            n.sub.D.sup.24                                                                            A 1.5643             144  2,4-Cl.sub.2                                                                         O  CH.sub.2CCCH.sub.2 Cl            n.sub. D.sup.24                                                                           A 1.5587             145  2,4Cl.sub.2                                                                          O  CH.sub.2CCCH.sub.2 OCH.sub.3                A                    146  4-Cl  O  CH.sub.2C CCH.sub.2 OCH.sub.3                                    147  4-Br, 2-Cl                                                                           O  CH.sub.2CH.sub.2CH.sub.2CH.sub.2 Cl                                                                             n.sub.D.sup.25                                                                            A 1.5627             __________________________________________________________________________

BIOLOGICAL EXAMPLES EXAMPLE I: (Pre-emergence)

Seeds of grasses were sown in pots and the surface of the soil was immediately sprayed with wettable powder formulations of the compounds of the invention in different concentrations. The pots were then placed in a greenhouse for 4 weeks. Thereafter the results were evaluated (as well as in the following examples) according to the scheme of Bolle (cf. Nachrichtenblatt des Deutschen Pflanzenschutzdienstes 16, 1964, pages 92 to 94):

    ______________________________________                                                 degree of damage in %                                                  number   weeds           crop plants                                           ______________________________________                                         1                 100                0                                         2        97.5     to <100    >0      to 2,5                                    3        95       to <97,5   >2.5    to 5                                      4        90       to <95     >5      to 10                                     5        85       to <90     >10     to 15                                     6        75       to <85     >15     to 25                                     7        65       to <75     >25     to 35                                     8        32.5     to <65     >35     to 67,5                                   9        0        to <32,5   >67.5   to 100                                    ______________________________________                                    

The herbicides Fluorodifen (4-Nitrophenyl-(2'-nitro-4'-trifluoromethylphenyl) ether and Mecoprop (2-(4'-chloro-2'-methylphenoxy)-propionic acid, used for comparison, were applied in the same manner. The results indicated in the following Table I shows that the compounds of the invention had a much better effect against grasses than the two comparative herbicides. The other compounds specified in the examples of preparation had a similar effect against grasses.

EXAMPLE II: (Post-emergence)

Seeds of annual grasses were sown in pots and allowed to germinate in the greenhouse. 3 Weeks after sowing the plants were sprayed with wettable powder formulations of the compounds of the invention in different concentrations and the results were evaluated after the plants had been kept in the greenhouse for 4 weeks.

Rhizome pieces or young established plants of perennial grasses, namely couch grass (Agropyron) and Bermuda grass (Cynodon), were transplanted into pots and grown for about 4 weeks whereupon, at a height of growth of about 10 to 15 cm, they were sprayed with the compounds of the invention.

The results were evaluated about 4 weeks after the treatment. In this trial, too, Fluorodifen and Mecoprop were used as comparative herbicides. The compounds of the invention were more effective against annual and perennial grasses than the two comparative herbicides (Table II). The other compounds of the examples of preparation had similar effects.

EXAMPLE III

Some of the compounds used in the preceding example were tested in pre-emergence and post-emergence trials in various crop plants. The result was evaluated after approximately 4 weeks (cf. Table III). It can be seen that even in a high concentration of 2.5 kg per hectare the compounds of the invention did no or very little harm only to a great number of important crop plants. The compounds of Examples 1, 2, 12, 13, 17, 21, 24, 27, 28, 29, 30, 32, 54, 55, 60, 61, 86, 94, 95, 99 and 102 had also a very good selective effect in the specified crops.

                  Table I                                                          ______________________________________                                         herbicidal effect in evaluation numbers                                        pre-emergence treatment                                                        Compound of                                                                             kg/ha.                                                                Example  A.S.    AGR      ALM   SAL  LOM   EGC                                 ______________________________________                                         13       2.5              2     2    1     1                                            0.6              3     4    2     1                                   32       2.5              1     1    1     1                                            0.6              3     3    2     1                                   33       2.5              1     1    1     1                                            0.6              3     5    2     1                                   94       2.5              1     1    1     1                                            0.6              2     2    1     1                                   102      2.5              1     2    1     1                                            0.6              2     3    3     1                                   61       2.5     5        1     1    1                                                  0.6              3     1    3                                         59       2.5     2        3     2    1     1                                            0.6              3     3    3     2                                   55       1.25             1     1    2     2                                            0.6              2     2    3     2                                   2        1.25             1     1    1     1                                            0.6              1     1    1     2                                   54       1.25                   2    2                                                  0.6                    2    4                                         17       5                1     1    1     1                                            1.2              2     1    1     2                                   86       5                      1    2                                                  1.2                    1    3                                         21       5                      1    1                                                  1.2                    1    2                                         1        5                      1    1                                                  1.2                    1    3                                         24       5                      1    2                                                  1.2                    3    3                                         29       5                      1    2                                                  1.2                    2    3                                         30       5                      1    1                                                  1.2                    1    4                                         36       1.25             1     1    1     1                                            0.6              2     2    1     1                                   99       5                      1    2                                                  1.2                    1    4                                         95       5                      2    2                                                  1.2                    3    4                                         12       2.5              1     1    1     1                                            0.6              3     4    3     1                                   28       5                      1    2                                                  1.2                    1    3                                         60       5                      1    2                                                  1.2                    1    3                                         27       5                      1    3                                                  1.2                    1    3                                         6        2.5              1     1    2     1                                            0.6              2     3    2     2                                   7        2.5     4        3     1    1     1                                            0.6              4     2    1     2                                   8        2.5              1     2    1     1                                            0.6              3     4    3     1                                   10       2.5              2     1    1     1                                            0.6              3     1    2     1                                   11       2.5              2     1    1     1                                            0.6              3     1    1     1                                   16       2.5              1     1    1     1                                            0.6              3     1    4     1                                   20       2.5              1     2    1     1                                            0.6              2     2    2     1                                   22       2.5              3     2    1     1                                            0.6              3     2    3     3                                   23       2.5                    1    1     1                                            0.6                    1    3     1                                   31       2.5     5        1     1    1     1                                            0.6              1     1    1     1                                   37       2.5              4     1    1     1                                            0.6              4     2    1     2                                   39       2.5              3     1    1     1                                            0.6              3     3    2     2                                   40       2.5              3     1    1     1                                            0.6              4     2    1     1                                   46       2.5              2     1    1     1                                            0.6              3     1    1     2                                   48       2.5              2     1    1     1                                            0.6              3     1    1     1                                   53       2.5              3     2    1     1                                            0.6              4     2    1     1                                   58       2.5              1     1    1     1                                            0.6              2     1    3     1                                   62       2.5              1     1    1     1                                            0.6              1     1    3     1                                   80       2.5              4     1    1     1                                            0.6              4     1    1     2                                   81       2.5              3     2    2     2                                            0.6              5     4    2     3                                   82       2.5              3     1    1     1                                            0.6              3     2    2     3                                   115      2.5                    1    2     1                                            0.6                    2    3     2                                   116      2.5              3     2    2     1                                            0.6              4     2    2     2                                   117      2.5              1     2    1     1                                            0.6              1     3    2     1                                   118      2.5              2     1    1     1                                            0.6              3     1    1     1                                   119      2.5              1     1    1     1                                            0.6              3     1    2     1                                   120      2.5              3     2    1     2                                            0.6              3     2    2     2                                   104      2.5              1     1    1     1                                            0.6              2     1    2     1                                   106      2.5              2     2    2     1                                            0.6              2     2    3     1                                   107      2.5              1     2    1     1                                            0.6              1     2    1     1                                   109      2.5              3     1    1     2                                            0.6              5     2    1     2                                   111      2.5              1     1    1     1                                            0.6              3     1    1     1                                   124      2.5              2     2    1     1                                            0.6              4     2    2     2                                   125      2.5              1     1    1     1                                            0.6              4     2    2     1                                   126      2.5              3     1    1     1                                            0.6              4     2    2     2                                   127      2.5              3     1    1     1                                            0.6              4     2    2     2                                   129      2.5              1     1    1     1                                            0.6              4     1    1     1                                   130      2.5              3     1    1     2                                            0.6              5     2    1     2                                   131      2.5              2     1    1     1                                            0.6              4     1    1     1                                   132      2.5              1     1    1     1                                            0.6              2     2    1     1                                   133      2.5     4        3     1    1     1                                            0.6     4        3     1    2     2                                   137      2.5              2     1    1     1                                            0.6              4     1    3     1                                   138      2.5                    1    1     1                                            0.6                    1    5     1                                   139      2.5              2     1    2     1                                            0.6              3     1    4     1                                   140      2.5              1     2    1     1                                            0.6              2     2    1     1                                   143      2.5              2     2    2     1                                            0.6              3     3    2     1                                   144      2.5              4     1    1     1                                            0.6              4     2    2     2                                   84       2.5              1     1    1     1                                            0.6              2     2    1     1                                   70       2.5     5        1     1    1     1                                            0.6              3     3    3     1                                   69       1.25             3          2     2                                            0.6              3          3     2                                   71       1.25             3          3     2                                            0.6              3          4     4                                   57       1.25             1          2     1                                            0.6              2          2     3                                   9        2.5              2     1    1     1                                            0.6              2     1    1     1                                   14       2.5              1     1    1     1                                            0.6              2     1    1     1                                   15       2.5              1     1    1     1                                            0.6              1     1    1     1                                   34       2.5              1     1    1     1                                            0.6              1     1    1     2                                   66       2.5              1     1    1     1                                            0.6              1     1    1     1                                   147      2.5              1     1    1     1                                            0.6              1     1    1     2                                   Fluorodifen                                                                             2.5     8        7     1    1     4                                            0.6     9        8     5    8     8                                   Mecoprop 2.5              4     3    5     3                                            0.6              7     6    8     7                                   ______________________________________                                          ALM = Alopecurus myosuroides                                                   SAL = Setaria lutescens                                                        LOM = Lolium perenne                                                           ECG = Echinochloa crusgalli                                                    AGR = Agropyron repens                                                   

                  Table II                                                         ______________________________________                                         Herbicidal effect in evaluation numbers                                        post-emergence treatment                                                       Compound                                                                       of                                                                             Example kg/ha A.S.                                                                               AVF     ALM   SAL  LOM   EGC                                 ______________________________________                                         13      2.5               1     1    1     1                                           0.6               1     1    3     1                                   32      2.5               1     1    1     1                                           0.6               1     1    1     1                                   33      2.5               1     1    1     1                                           0.6               1     1    1     1                                   94      2.5               1     1    1     1                                           0.6               1     1    1     1                                   102     2.5               1     1    1     1                                           0.6               2     1    2     1                                   61      2.5               2     1    3     1                                           0.6               3     1    6     1                                   59      2.5                     1    1     1                                           0.6                     2    3     1                                   55      2.5                     1    1     1                                           0.6                     1    3     3                                   2       5                       1    1                                                 1.2                     2    3                                         5       2.5                     1          1                                           0.6                     1          1                                   43      2.5                          1     1                                           0.6                          4     6                                   44      2.5                                1                                           0.6                                5                                   45      2.5                          1     1                                           0.6                          6     6                                   52      1.25      1                        1                                           0.6       1                        1                                   64      0.6                                1                                   72      2.5                          1     1                                           0.6                          3     4                                   77      0.6                                2                                   78      2.5                                1                                           0.6                                8                                   79      2.5                          1     1                                           0.6                          7     6                                   87      0.6               1                1                                   96      0.6       1                        1                                   97      2.5       1             1    1     1                                           0.6       4             2    1     1                                   101     0.6                                1                                   103     0.6               5                1                                   4       0.6               1                1                                   26      0.6       5                        1                                   42      0.6       5                        1                                   1       0.6       3                        1                                   17      0.6               1                1                                   21      0.6                                1                                   24      0.6                                1                                   27      0.6       3                        1                                   28      0.6       3                        1                                   29      0.6       2                        1                                   30      0.6       3                        1                                   36      2.5       4             1    1     1                                           0.6       5             1    1     1                                   54      0.6               1                1                                   60      0.6               1                1                                   86      0.6               1                1                                   95      0.6                                1                                   99      0.6                                1                                   12      2.5               1     1    1     1                                           0.6               1     1    3     1                                   Fluorodifen                                                                            2.5               8     2    6     4                                           0.6               8     3    8     6                                   Mercoprop                                                                              2.5               8     7    8     8                                           0.6               9     8    9     9                                   ______________________________________                                          Key for weed grasses of Table II                                               AVF = Avena fatua                                                        

                  Table III                                                        ______________________________________                                                         dosage in kg/ha                                                tolerability by crop plants                                                                    A.s. NA =                                                      VA = pr-emergence                                                                      Example 33                                                                               Example 59 Example 36                                                2,5       2,5        2,5                                               type of crop                                                                             VA      NA      VA   NA    VA     NA                                 ______________________________________                                         sugar beet                                                                               1       1       1    3     1      1                                  sunflower 1       1       1    1     1      1                                  rape      1       1       1    1     1      1                                  white cabbage                                                                            1       1       1    1     1      1                                  cucumber  1       2       1    1     1      1                                  peanut    1       1       1    1     1      1                                  soybean   1       1       1    1     1      1                                  kidney bean                                                                              1       1       1    1     1      1                                  pea       1       1       1    1     1      1                                  horse bean                                                                               1       1       1    1     1      1                                  cotton    1       3       1    4     1      1                                  tomatoe   1       1       1    1     1      1                                  tobacco   1       1       1    1     1      1                                  carrot    1       1       1    1     1      1                                  wheat     1       2       1    1     1      1                                  ______________________________________                                     

What is claimed is:
 1. A 2-[4'-phenoxyphenoxy]-propionic acid derivative, or a salt thereof with a base, of the formula ##STR78## in which R means identical or different substituents selected from the group consisting of halogen, C₁ -C₄ alkyl or C₁ -C₄ alkoxy;n is 1 or 2; Y is oxygen or sulfur; R₁ ' is a linear or branched C₁ -C₄ alkylene; and R₅ represents C₁ -C₆ alkyl, C₁ -C₄ haloalkyl, C₂ -C₈ alkoxyalkyl, C₃ -C₁₂ alkoxyalkoxyalkyl, hydroxyethyl, phenyl or phenyl substituted once or twice by halogen and/or C₁ -C₃ alkyl.
 2. The compound defined in claim 1 which is 2-[4'-(2",4"-dichlorophenoxy)-phenoxy]-propionic acid 3-methoxy-n-butyl ester.
 3. A herbicidal composition containing from about 2% to about 95% by weight of a compound as defined in claim 1 as the active ingredient.
 4. A herbicidal composition containing from about 2% to about 95% by weight of a compound as defined in claim 2 as the active ingredient.
 5. 2-[4'-phenoxyphenoxy]-propionic acid derivatives of the formula ##STR79## in which R is selected from the group consisting of halogen, C₁ -C₄ alkyl and C₁ -C₄ alkoxy,Y is oxygen or sulfur, n is 1 or 2 and R₁ is alkoxyalkyl.
 6. An herbicidal composition containing as an active ingredient a compound as defined in claim
 1. 